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Fluorescent probe for detecting hydrogen sulfide in endoplasmic reticulum

A fluorescent probe and hydrogen sulfide technology, applied in the field of fluorescent probes and organic small molecule fluorescent probes, can solve the problems of cumbersome operation, inability to monitor hydrogen sulfide transient reaction in time and space, cell and tissue sample destruction, etc.

Inactive Publication Date: 2017-10-27
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the hydrogen sulfide detection methods reported at home and abroad mainly include colorimetry, electrochemical analysis, gas chromatography and sulfide precipitation, etc. However, these techniques cannot monitor the transient reaction of hydrogen sulfide in time and space, and the The preparation process is cumbersome and requires irreparable damage to cell and tissue samples

Method used

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  • Fluorescent probe for detecting hydrogen sulfide in endoplasmic reticulum
  • Fluorescent probe for detecting hydrogen sulfide in endoplasmic reticulum
  • Fluorescent probe for detecting hydrogen sulfide in endoplasmic reticulum

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of compound N-(2-aminoethyl)-4-methylsulfonamide (3):

[0033] ;

[0034]At 0°C, add 10 mmol ethylenediamine (1) and 20 mL dichloromethane into a 100 mL round-bottomed flask, add 30 mmol triethylamine under stirring, stir the resulting solution for 10 min, then add 5 mmol A solution of p-toluenesulfonyl chloride (2) in dichloromethane (3 mL). Then warm to room temperature and stir for 10-12 hours. Then, 20 mL of 10% sodium carbonate aqueous solution was added to the reaction to quench the reaction, and then 20 mL of dichloromethane was added to the reaction system. After the entire reaction system was washed with water three times, the organic phase was dried with anhydrous magnesium sulfate. Dichloromethane was distilled off under reduced pressure to obtain a white powder crude product, which was separated by column chromatography (petroleum ether / dichloromethane=50:1 to 10:1), and recrystallized with ethanol to obtain a white solid product N-(2-amino Et...

Embodiment 2

[0043] Hydrogen sulfide fluorescent probe Na-ER-H 2 Ultraviolet-absorption detection of the interaction between S and hydrogen sulfide

[0044] After adjusting the baseline of the UV-absorption-visible spectrophotometer with the blank solution, put 5 μM probe PBS solution containing 5% DMSO, and then add an appropriate amount of sodium sulfide aqueous solution to make the final concentration of sodium sulfide 200 μM. The UV-absorption curves of the interaction between the probe and hydrogen sulfide were tested at different times. Depend on figure 2 It can be seen that as time goes on, the absorption peak at 370 nm (the absorption peak of the probe itself) gradually decreases, while the absorption peak at 445 nm (the absorption peak of the reduced product after the probe interacts with hydrogen sulfide ) gradually increased.

Embodiment 3

[0046] Endoplasmic reticulum hydrogen sulfide fluorescent probe Na-ER-H 2 Selectivity test for S

[0047] Solution preparation: make the mother solution concentration of relevant substances to be detected: 100 mM, including: various common anions and cations, amino acids, active oxygen and nitrogen substances; make a DMSO solution with a concentration of 1 mM probe as the test mother solution.

[0048] Preparation of test solution: Measure 15 μL of probe mother solution and 135 μL of DMSO, use PBS buffer to make the volume to 3 mL, and then add an appropriate amount of analyte (so that the concentration of the analyte is: active oxygen, active nitrogen 100 μM; ion and amino acid 2.5mM), shake well and perform fluorescence detection with a fluorescence spectrometer (λ ex = 445 nm, λ em = 543 nm), and make a fluorescence intensity histogram according to the moral fluorescence curve of image 3 ),Have image 3 It was found that this fluorescent probe specifically recognizes...

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Abstract

The invention provides a fluorescent probe for detecting hydrogen sulfide in endoplasmic reticulum. The chemical name of the fluorescent probe is 4-azido-N-(2-aminoethyl-4-methyl benzene sulfonamido)naphthalimide, or Na-ER-H2S for short, and the molecular formula is C21H17N5O4S. The invention further discloses the response of the fluorescent probe to hydrogen sulfide in cells, and the endoplasmic reticulum positioning effect is very good. Accordingly, the fluorescent probe provided by the invention can be utilized for detecting hydrogen sulfide in the cells or other biological samples through fluorescent imaging.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting hydrogen sulfide in the environment and the endoplasmic reticulum in organisms, and belongs to the technical field of organic small molecule fluorescent probes. Background technique [0002] Hydrogen sulfide (H 2 S) is a colorless gas with the smell of rotten eggs. It has always been recognized as a chemical pollutant. Long-term exposure to hydrogen sulfide can cause damage to the respiratory system. Excessive inhalation of hydrogen sulfide gas can cause loss of consciousness, shock, and even death. However, medical research has found that hydrogen sulfide plays an important physiological function in the metabolism of organisms, especially in the cardiovascular system and nervous system. After carbon monoxide (CO) and nitric oxide (NO), it has become the third important endogenous Genetic gas signaling molecules. Endogenous hydrogen sulfide is produced by the enzymatic reaction of sulfur-con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/6428G01N2021/6432
Inventor 林伟英唐永和徐安马燕燕
Owner UNIV OF JINAN
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